20 Must-Follow Rules for Men Who Want to Dress Well

You never grew up with much interest in personal style, and you never developed a natural instinct for how you should dress. And even though you can find a ton of information online, it confuses and overwhelms you more than it helps you understand.

And it sucks, doesn’t it?

Because you’re a smart man, and you should be able to figure this out. You just have no clue where to start.

You have no clue what to focus on.

But you know what?

You’re Not the Only Guy Struggling to Figure Out How to Dress Himself Better

Many guys struggle with it.

In fact, just a few years back, I struggled as well.

I was a terrible dresser.

And when I decided to step up from hoodies and graphic tees to something more respectable, I had a hard time figuring out how to dress well.

But despite all my early failures, I kept trying, and eventually things started to click in my head. I had to try out lots of terrible fashion tips before I found the nuggets that actually worked, but eventually, I developed a much better dress sense. Just see for yourself:

I could feel ashamed of the many years spent dressed like a slob. But instead, I feel proud.

Because I had zero style sense. I had to learn how to be a well-dressed man. And when I consider where I came from and where I am now, I’m proud of how far I’ve come.

And any man can do what I did, no matter where they’re at now.

You can do it too.

And with some guidance, you can do it a lot quicker than I did.

How to Dress Well: The 20 Rules Every Beginner Should Follow

You can figure this out.

You can improve that dress sense of yours.

And once things start clicking in your head, it will actually become easy. You just need a bit of guidance at first, so you’re focused on the right things.

So I took the most important lessons that I’ve learned over the years and put them into this article.

These are the guiding rules that all style rookies should follow.

Just imagine an empty wardrobe. What are you gonna fill it up with?

Rule #1: Start From Scratch

When you want to start dressing with style, you have to start from the beginning.

That doesn’t mean you should discard of all your clothes right away. (I’m fairly sure society frowns upon naked men going clothes shopping.)

But, you should accept that you will eventually get rid of most of your current wardrobe. You will trade it in for one that’s better suited and more refined, even if you still want to keep it casual.

Saying goodbye to some of your favorites will be hard, but it must be done in order to make progress.

But don’t worry; you’ll get new favorites.

You’ll get better favorites that will make you look way more awesome.

Rule #2: Forget Everything You Think You Know

One of the hardest things I ever had to accept was that my fashion-knowledge was nonexistent.

During my researching stage, I would often read something that completely flipped my world upside down.

Things I deemed inconsequential turned out to be of vital importance, while things that I thought were crucial turned out not to matter at all.

You should accept that you may not know as much as you think.

You should think of yourself as a complete beginner, so you don’t gloss over anything that could help you see the light. Otherwise, you’ll likely skip important lessons.

Assume you know nothing, and you’ll be open to learn everything.

You Can’t Get More Basic Than a Plain White Tee

Rule #3: Focus on the Basics

So now that you’ve forgotten everything you knew, what do you think you should focus on first?

The basics, of course.

Mastering the basics alone will benefit you greatly. I always say it’s half the battle, but it’s more like three quarters, if not more.

Too many men shoot themselves in the foot by getting the basics wrong.

Rule #4: Build a Solid Wardrobe Foundation

You need to collect versatile wardrobe staples that match well with almost anything — basic items like white shirts, dark blue jeans and grey sweaters.

Items like these will serve as training wheels while you learn to get the basics right. They’ll also keep you safe from making mistakes when you don’t know how to match clothes yet. (And after you’ve built your foundation, you can add more eye-catching clothes to your wardrobe, and you’ll always have items in your wardrobe to wear them with. )

Rule #5: Keep it Simple

You have to remember that you’re a man, and being extravagant isn’t necessary. You don’t need a lot of bells and whistles to look great.

You can just keep everything simple.

Leonardo DaVinci once said, “Simplicity is the ultimate sophistication.”

Keep this in mind when you’re putting your outfit together. Stop over-complicating things. Simple style is the best style for guys.

Rule #6: Fit Comes First

Unfortunately, most guys get this wrong, and getting this wrong sabotages anything else you try.

I mean, just compare these two shirts:

The difference between good and bad fit

Which do you think looks better?

The shirt on the right completely throws off my body’s proportions, making me look like I raided someone else’s closet.

Dressing well is all about the fit, guys.

Fit comes first.

If you only follow one rule from this article, follow this one.

Rule #7: Trim Your Wardrobe

Having a bulging wardrobe offers no benefit.

In fact, having lots of clothes in your wardrobe is impractical. (Which is good news for guys who are trying to build a wardrobe on a budget!)

You want to keep your wardrobe trim.

Never fill your wardrobe up with lots and lots of clothes, thinking this will offer you variety. You won’t need lots to have a great arsenal of stylish outfits. You’d be amazed at how few you really need.

Also, you should prune your wardrobe periodically for items that look washed out, that no longer fit or that you simply no longer wear. You should discard these items and keep your wardrobe decluttered.

Rule #8: Expand Your Options

You don’t want to be that guy that wears the same outfit day in and day out. You need a bit of variety.

But that doesn’t mean you should look like you didn’t bother. Your clothes must still look good on you and they must work together in a way that’s pleasing to the eye..

You still want to look like you know what you’re doing.

Expand your comfort zone

Rule #12: Try New Things

When you’re developing your sense of style, you want to open your mind to new types of clothing and clothing styles. You should try things you never would have thought to wear before.

Maybe you try wearing chinos instead of jeans or a jacket instead of a sweater. Maybe you can try business casual attire or even a suit. Maybe you can try changing your sneakers for desert boots, loafers or brogues.

You’d be amazed how good you could look in items that you previously thought “weren’t you.”

Trying on everything and anything will teach you more about your personal style than all the style and fashion blogs combined.

Rule #13: Learn to Love Colors

Most males don’t seem to like wearing colors that much. Many of us stick to a basic color scheme of black, white, grey and blue.

If that sounds like you, you want to expand your color horizons.

You have to figure out which colors work for you, and the best way to do this is to try them out. (See previous rule.)

Colors can make an outfit pop, so you should never shy away from them.

Start With 1 Color at a Time

Rule #14: Wear Colors Sparingly

While you should learn to love colors, you want to avoid wearing too many of them at the beginning of your style journey.

You’ll risk wearing incompatible colors, since you probably don’t know how to match them yet.

Stick to just wearing one color at a time for now, and keep the rest neutral. Once you’re further educated you can start trying to combine them.

Rule #15: Laugh Off the Jabs

When you start improving your style, you’re guaranteed to receive a few jabs from your friends.

The secret to dealing with this is not to care and laugh it off. Just crack a joke about it yourself. That way you’ll be in on the joke, instead of the butt of it.

Eventually your friends will get used to the new you, and the jokes will cease.

Rule #16: Be Open to Feedback

You may also have people in your life that will genuinely try to help you, so be open to their advice.

Consider the person the advice comes from and what they have to say.

Usually, you can tell when a criticism is genuine, or when someone is just trying to cut you down a few inches.

Hint: People who provide sincere counsel will usually be people that dress fairly well themselves.

You should also listen to the women in your life, as they often are happy to give their honest feedback (although they can also be too supportive).

Rule #17: Be Honest With Yourself

You never want to look like someone that you’re not. You’ll feel incongruent when you sport a look that doesn’t fit with your personality.

If you’re a an introvert, wearing extremely loud outfits will seem weird.

If you’re a laid-back type of guy, you may not want to walk around in formal suits all the time.

Simply aim to look like a better dressed version of yourself.

Style reinvention takes time. There’s no rush.

Rule #18: Accept That it Will Take a While

Your sense of style is like Rome; It won’t be built in a day.

You’ ll need a while to fully grasp all the little intricacies that make an outfit great.

Personally, I spent years learning and experimenting, before I could put everything together. It took me a long time to discover a look I was satisfied with, mostly because very little I tried actually helped me.

Don’t expect to become a better dresser within a month or two. You should prepare to spend some time on it.

Rule #19: Accept That You Will Make Mistakes

We all make mistakes. None of us are immune to this. I still make mistakes to this day.

Look at celebrities.

They often have personal stylists or designers creating clothes just for them to wear, and the clothes they wear are judged under a microscope.

They make mistakes, but it’s because they try new things. Sometimes it works; sometimes it doesn’t.

This shouldn’t keep you from trying new clothes.

The road to success is paved with mistakes. You just need to realize when you’ve made one, accept it and move on.

Eventually, it will all make sense

Rule #20: Know That You’ll Get There Eventually

If you keep working on it, eventually you’ll train your eye for style.

You’ll notice details in your own and other people’s outfits. You’ll know when something works and when it doesn’t. Selecting a great outfit from your closet will be as easy as riding a bike.

No matter how much you’re struggling, take comfort in the knowledge that you’ll get there eventually.

Follow These Rules and Develop Your Sense for Dressing Sharp

Following these 20 rules will help you build a kick-ass style, but you will have to work on it.

Change never comes from reading things; it comes from taking action.

So if you’re serious about taking your style to the next level, pick one small thing you want to improve, and work yourself up from there. (I recommend starting with #6)

Pick one thing, and then focus on mastering that one thing. Then, pick the next, and the next, and the next.

Slowly but surely, you’ll start to see major improvements. Slowly but surely, you’ll developed your sense of dressing well. Slowly but surely, you’ll create a look that kicks ass.

And then, you’ll notice that you feel better about yourself, that you get more respect, and that you catch more attention from the ladies.

Because that’s what a kick-ass style will do for you.

And all you need to do is follow these rules, focus on on the right things, and take one small step at a time.

Comments

I took your advice and bought a couple of new pairs of dark blue jeans that fit great. Now that I finally found great fitting jeans, I’d like to pick up a couple more pairs. Do you still advise against lighter colored jeans? I need more than 2!
Thanks!
Dave

Hi, this is a great article, but I have one thing I’d like clarified.
You say to dress like a ‘better version of yourself’, what does that mean exactly?

Also, since I’m on a budget, how do you go about buying new clothes? You say not to wear the same outfit over and over again but what if it’s 6 months of saving before I can get four or five different outfits?

It means dressing like yourself, but making sure your clothes fit, look good on you and are well-matched.
If you’re on a budget, just take it one step at a time.You don’t need a ton of clothes to create different outfits. Check out this and this article.

I loved your article about clothing but i do have a few questions for dressing very sharp or business casual. What colors would be good to blend together and also how do i break the habit of wearing skinny jeans a hoodie and some vans? Is this good casual street style because i would like to transition into a more sharp defined look

This article is amazing, and really easy to read and understand. Thanks for sharing it and help us on this journey. Do you have some advice for someone in his early 20’s (21atm) to ease the transition?

This is by far the best article on how to dress like a man, yet stay true to yourself I have ever seen. Thank you so much for actually laying out letitment ways to improve ones style. I have strugled for years to find my own style and no one has given me advise I can actually follow. I was starting to give up hope on finding a syle that fits me, but now I understand the basics of dressing better. My confidence that I will eventually get there has sky rocketed and I feel like this is now something I can grasp and accomplish

Totally loved the article Robert! I’ve been sorta black-grey-white guy, maybe it’s time to play with some colors. I agree with you, I does pops out, makes you look little bit interesting and creative. Learning the art of using color wheel can be tremendously helpful. Thanks for the advice, I’ll keep you posted :)

Good article. The one part I didn’t agree with is choosing color to stand out from other guys. I find that most men wear color in an attempt to not look boring but in turn end up looking like every other guy. It’s actually rare to see a guy who wears just black white and grey. At least where I’m from. I think those are the best color choices because they evoke sophistication and you can never go wrong with them. But that’s just my opinion.

I have been enjoying your simple and easy-to-understand articles. I’m thinking about buying your ebook now, I’m hoping it will give me more information on topics I’m almost clueless about(how to layer clothing, how to choose the colors of your clothing wisely ect.) Keep up the good work.

His book us awesome. It saved me hundreds of hours of research. Within a month of implementing his suggestions in the book I started to get compliments. Without fail, every week since somebody tells me how sharp I’m looking. Better than that, I love the new look.

Hello sir,
Good article and also useful for me but I have some problem, when I choose colour I totally confused 😕 which type of colour suit for me. My face is light brown colour. Can you suggest me plz best choose for me both shirt and jeans

micheal,i think you can develop your eye for good things by trying to admire a neat shirt or well ironed shirt on somebody’s body..try to compare it to yours and get the difference between the two…try to admire colours like blue,red,purple, shirts mixed with dark and bright colours….tell yourself good things about them and maybe admire the button,collar and pocket shapes if yours dont have the same…nd try buying things from a different place..

I found your ideas very interesting. I’ve been in such a path for about 2 years. Now I think I found the way, and it is so much surprising that the right way is just to make everything as simple as possible! Today all I have is: 1 suit, 7 modal T-shirts, 2 dark jeans, 2 khaki pants, 5 polos, 12 dress shirts, 3 dress pants, 3 oxford shoes (2 black and 1 brown), a moccasin, one pair of informal leather shoes, 1 jeans jacket, 1 leather jacket. I’m now looking for 2 sweaters. And that is all I need! Everything fits perfectly, and is very good quality. The dress shirts and the suit were made to measure. The polo shirts and T shirts are all slim-fit. The dark jeans and the khaki pants are also slim-fit. Everything is in sober colors (except for a red polo shirt, but it is said that people in red are percieved as more attractive!). All my dress-shirts are plain white or blue. I’m really satisfied with my wardrobe now!

Hello sir
Thanks a lot for this awesome post.
But my problem is this that i find unable myself to select best dress for me. I became helpless to choose good colour which gives me smartlook.please give me some suggetion.

Hello sir Thanks a lot for this awesome post.
But my problem is this that i find unable myself to select best dress for me. I became helpless to choose good colour which gives me smartlook.please give me some suggetion.

Hey Robert. I like your article. My problem is that I like feeling comfortable and that kills me. I usually go to work in sweat gear and then I go to the gym. Even though I go to the gym I have a bulky figured. I hate shoes that give me foot pain so I used sneakers and sometimes shoes that don’t hurt my feet. What’s your suggestion for feeling comfortable and fashionable at the same time.

here’s a confession: I love lounging around the house in my sweatpants. So comfy! And I can imagine if that’s what you’re used to wearing all the time, almost everything else will feel a bit uncomfortable when you first try it. But it’ll just take some getting used to. If you keep wearing well-fitted jeans for a while, it becomes the new normal.

They won’t be quite as comfortable as sweatpants, but you’ll actually feel better about yourself because you’re putting your best self forward :)

Very interesting article. I’m opening up my sense of style by trying some of the things you mentioned. Even though its a new journey for me I find this article very helpful. I struggle with looking through my closet and seeing many graphic T-shirts not enough or any dress shirts or collar shirts to layer with blazers etc. I do have a sense of style somewhat but this time around i want to change completely so I’m looking for more stylish clothing and wearing clothes I never thought I would along with shoes. Apart from looking more attractive I want to look like I mean business when I walk into the room. Although, I’m sure this will all come together with time.

as I mentioned in my replies to your previously left comments, most of this is just because you haven’t yet developed an eye for what looks good and what doesn’t. This article is meant to give you a broad overview of what you need to know/learn. Nobody can explain everything it takes to develop a better sense of style in just one blog post. It would need to cover too much information. Heck, I wrote an e-book on the subject that’s 200+ pages long, and that still only focuses on the information that matters most.

If you want more detailed explanation, you should check it out. You can also check out some of my other blog posts that hone in on more specific aspects.

Sorry Michael, I’m not sure what you’re expecting from me here. I can’t show you how to develop your eye in the space of a comment or a blog post. It takes time and practice. Though, if you want to make it easier on yourself, you get some guidance.

If you want to develop your eye for style and you don’t know where to start, then I would highly suggest my e-book. It breaks everything down into tiny steps, giving you a clear roadmap so you only have to focus on and understand one thing at a time. I get tons of feedback from guys who were in the same (or similar) situations as you that it helped “open their eyes.”

I hate being all salesman in my comments section, but I truly believe that might be your best option (and there’s a money-back guarantee if you’re still unsatisfied).

And if you don’t want to pay for the information, there’s still plenty useful advice to be found on the rest of my site. Another good place to start ;)

good question! Sure there is. I think as you develop a biut more understanding on what looks good on you and what doesn’t, you develop “favorites”, i.e. you can distinguish that one items looks better on you than another.

Just like you’ll be able to distinguish that one color looks better on you than another. You just need to develop your eye for it a bit.

a polo some chinos or jeans and maybe some dress shoes or air forces. Maybe some vans if your going casual but ultra casual would be some designer jeans a designer belt some jordans or good looking air forces and a hoodie with designer brand. If you just wanna look smart business casual get yourself a polo a sweater jeans or chinos and some dress boots or just shoes.

Great article! imo, no. 5 & 12 are the most true!
However if you stay simple(no.3) you just wont stand out of all the other guys…
lol guys maybe you got some opinions, ever tried moennlondon.com? not sure if worth it…

Great piece Robert! I especially love the parts on keeping it simple and understanding that it will take time.

For me, it took me along time to realize that keeping it simple was such an important part of style. Like most things in life, style can really be boiled down to some simple principles.

To this list I might add, “Find a reliable brand”. At first, I thought I had to own a wardrobe containing tons of different brands. After a while I found that J. Crew clothes, for the most part, are always the best option fit and style-wise.

Great post! Improving my style improved my life in a very similar way as it did for yours. It took me a few years to get everything down and most of what I learned is taught in these twenty tips. Way to save everyone a ton of time!

You really should make it an option to pay for guides etc with paypal. I would guess a lot more then me are sceptical to hand out credit card info on sites, but to donate a few bucks with an excisting paypal account is easy :)
(I was about to buy the color matching ebook, but …)

I certainly understand your frustration. I wanted to give the color matching guide for a pay-what-you-want pricing, which to my knowledge was only possible this way. Though, I’ve recently been looking into alternatives.

Hello Robart actually my body is sooo fat can you suggest me which type of dress make me cool. I want to be cool parson because in my friend circle I m looking very ode as I think can u suggest me which dressing sense is parfect for me?

Hey Robert nice reading this IVE been feeling lost from the start on how to start dressing nicer im 20 but I’m 5-5 and sometimes I feel like I’m still young as in high school still cuz I’m so short. Anyways I’ve seen how to dress properly and get an idea but where could I find motivation and change my mindset that I’m no longer in high school. And also im skinny as well and I see all these good dressers that a tall and muscular and usually in stores they are for taller people. I’m wondering if there’s a way to dress for short people if there is or just trying to find small sizes for the nice wardrobe clothes. Thanks

So I was wondering if you could give me some advice on plaid button up dress shirts. I’m 6’5″ and have a 6’9″ wingspan. When I try on shirts that are long enough for my arms they’re usually too baggy for my slim figure, but on the other hand if I find something I feel works for my figure I do the length test and the sleeves are always too short and when I stretch my arms out fully the bottoms of these shirts become untucked. How do I find a L or XL dress shirt, that’s long enough and won’t come untucked when I fully extend my arms? Thanks.

I have similar problem as yours. (And pretty much any guy hs his own specific set of problem with finding well-fitting shirts.)

So what you want to do is go for the shirts that are long enough, and then get them slimmed down by a tailor. This is what I do with almost any shirt I buy, and I’m sure you’ll be quite happy with the result.

Great plan. I worked for several retail clothing stores and was bummed that the opportunities never lasted. My wardrobe was usually horrible and scarce since I was usually out of shape and in child support debt. I have the idea, it’s everything else that’s bothering me into looking terrible. Now that there are a couple of interviews here and there, I’m on the rise again but nothing until there’s money in my pocket or something to do serious damage with. Still going to try. Peace, Health.

Hey Robert, I wanted to ask you a difficult question about dressing stylishly. I work outside in a warehouse…. in texas. But I still want to look good, however since temperatures reach 100+ with no air conditioning it seems like no matter what I do, even if i change clothes for lunch I will still stink.

Recently I have just been wearing a short sleeve button down untucked and shorts with some tennis shoes, are there any other work appropriate options I might try for summer times? (because right now i look and smell like a high schooler with a beard)

Also, for the winter I feel like I rely too much on my coats and winter accessories to look good. Luckily I can follow most of your guide throughout the winter since it will be cold enough for me to wear nicer clothing .

I have a sweaty friend who has been using a product called Odorex Extra Dry, and it works wonders according to him. Best thing, you only have to apply it 2-3 times a week. I haven’t personally used it yet, but maybe you should give it a try.

the clothes you wear can make you feel like a different person. Looking great makes you feel great, and you just become more confident and positive overall. It’s a process though, so don’t expect magic to happen.

I recently wore…a dark blue jeans with maroon formal shirt and a lemon yellow broad formal tie( with some maroon and yellow design)…i want to know if this matching was good…and does formal shirt and tie looks good with jeans…??

Hello Rob! my wardrobe usually consists only of v/round necked t-shirts, with jeans that fit my legs, i rarely put on jackets or suits, it is usually very hot where i live so multiple clothes are an option only in the winter, which i tend to keep light with just a Hoodie on top of my Tees…now all that being said, what can i improve on? (halp plx

I would add to that list that you should consider the climate you live in. For example if you live in Canada or the North East. Your wardrobe essentials now become more numerous and onerous. Instead of an expensive shoe you may want to invest in a quality dressy brown boot with a synthetic sole and look at the shoe at the end of Spring. Pay attention to the season you start your capsule… Cheers

Hey,
I’ve just found your site and loving it!
It’s always a pain looking for clothes, because I’m not slim. Often things I try on only accentuate this fact. My ultimate goal is to walk away from hoodies, of which I have two that I wear on my regular basis. Going into university this year, I want to transform the way I appear so I’m not ‘that guy’ at Uni, if that makes sense. I will definitely be trying more on though, that was a great suggestion!

I m 23, sim, weighing 64, 5ft 11inches.
Being a sailor I have not got time to see myself how I m and who I am
Because life was in academy only. But now as I m I look to myself
I feel I m not confident, the reason is I don’t know what to wear .
There are many people giving different views so it is difficult what to choose.
Some times I don’t go out for party or any occasions because I don’t have clothes.
I don’t buy because I don’t know what to wear.

I usually go more alternative to my outfits because that’s who I am, I’m very open to new things but I’m very shy and self criticizing. Is there any advice you could bestow upon me that might help with my situation? and as a side note I do tend to where clothes that are comfortable that’s my biggest concern. Any help will be appreciated :)

I am 17 and i have an image of always being relaxed all the time. I always wear jeans n nly jeans with simple checkered shirts n polo. Rule 12 is what i needed because i was extremely bored with my style. This link is super awesome. I wanted my restyling process to be cost efficient. The problem with me is colour match. I wear dark n dull or plain white colour. Help me out with colours.

I know that you mentioned white shirts, dark blue jeans, grey sweaters and black shoes, but what if I just altered one thing in this list? Could I replace those black shoes for chukkas or desert boots perhaps? What would you recommend?

Very glad I found this link! I’ve been working on upping my style for a while now, since coming to terms with the fact that I was going to be working in IT for a while yet so I wanted to stand out from my torn jeans and t-shirt wearing coworkers.

To make this journey more interesting, and to hit on a topic you don’t cover, I’ve lost 80+ lbs and counting over the last 2 years. Trying to find pieces that polish my new style, stay in budget, and don’t make me cry when I shrink out of them has been touch and go to say the least.

I’ve settled into a closet that works for me for now, and I have a list of items I will be adding once I reach my goal size and know I’ll be able to keep them around for years.

Yes! Number 1 and 15 ring true for me especially. Don’t worry about the naysayers. They’re just jealous that you have the balls to grow your style while they keep wearing those American Eagle cargo shorts from college.

Awesome post man. Very helpful. In particular, I have struggled with feeling overwhelmed when it comes to choosing new clothes. I am basically as beginner as is possible. But sometimes I think I try and get too creative. Like you say, I need to start with the basics.